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    Claisen Condensation

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    yash
    The Claisen condensation reaction forms a carbon-carbon bond between two esters or an ester and a carbonyl compound in the presence of a strong base to form a β-keto ester or β-diketone. At least one reactant must be enolizable by deprotonation to form an enolate anion. The base removes an alpha proton to form the enolate which then nucleophilically attacks the carbonyl carbon of the other reactant. The alkoxy group is eliminated, regenerating the alkoxide base which removes a doubly alpha proton to form a new stabilized enolate and the final product after acid workup.

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    Claisen Condensation

    Uploaded by

    yash
    167 views1 page
    The Claisen condensation reaction forms a carbon-carbon bond between two esters or an ester and a carbonyl compound in the presence of a strong base to form a β-keto ester or β-diketone. At least one reactant must be enolizable by deprotonation to form an enolate anion. The base removes an alpha proton to form the enolate which then nucleophilically attacks the carbonyl carbon of the other reactant. The alkoxy group is eliminated, regenerating the alkoxide base which removes a doubly alpha proton to form a new stabilized enolate and the final product after acid workup.

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    Claisen Condensation

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    The Claisen condensation reaction forms a carbon-carbon bond between two esters or an ester and a carbonyl compound in the presence of a strong base to form a β-keto ester or β-diketone. At least one reactant must be enolizable by deprotonation to form an enolate anion. The base removes an alpha proton to form the enolate which then nucleophilically attacks the carbonyl carbon of the other reactant. The alkoxy group is eliminated, regenerating the alkoxide base which removes a doubly alpha proton to form a new stabilized enolate and the final product after acid workup.

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    © All Rights Reserved
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    167 views1 page

    Claisen Condensation

    Uploaded by

    yash
    The Claisen condensation reaction forms a carbon-carbon bond between two esters or an ester and a carbonyl compound in the presence of a strong base to form a β-keto ester or β-diketone. At least one reactant must be enolizable by deprotonation to form an enolate anion. The base removes an alpha proton to form the enolate which then nucleophilically attacks the carbonyl carbon of the other reactant. The alkoxy group is eliminated, regenerating the alkoxide base which removes a doubly alpha proton to form a new stabilized enolate and the final product after acid workup.

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    of 1

    Mechanism of Claisen Condensation

    Claisen Condensation
    The Claisen condensation (not to be confused with the Claisen rearrangement) is a carboncarbon
    bond forming reaction that occurs between two esters or one ester and another carbonyl
    Reactioncompound in the presence of a strong base, resulting in a -keto ester or a -diketone. It is named
    after Rainer Ludwig Claisen, who first published his work on the reaction in 1887

    At least one of the reagents must be enolizable (have an -proton and be able to undergo
    deprotonation to form the enolate anion). There are a number of different combinations of
    enolizable and nonenolizable carbonyl compounds that form a few different types of Claisen
    condensations.

    The base used must not interfere with the reaction by undergoing nucleophilic substitution or
    addition with a carbonyl carbon. For this reason, the conjugate sodium alkoxide base of the
    alcohol formed (e.g. sodium ethoxide if ethanol is formed) is often used, since the alkoxide is
    regenerated. In mixed Claisen condensations, a non-nucleophilic base such as lithium
    diisopropylamide, or LDA, may be used, since only one compound is enolizable. LDA is not
    commonly used in the classic Claisen or Dieckmann condensations due to enolization of the
    electrophilic ester.

    The alkoxy portion of the ester must be a relatively good leaving group. Methyl and ethyl esters,
    which yields methoxide and ethoxide, respectively, are commonly used.

    Mechanism
    In the first step of the mechanism, an -proton is removed by a strong base, resulting in the
    formation of an enolate anion, which is made relatively stable by the delocalization of electrons.
    Next, the carbonyl carbon of the (other) ester is nucleophilically attacked by the enolate anion.
    The alkoxy group is then eliminated (resulting in (re)generation of the alkoxide), and the alkoxide
    removes the newly formed doubly -proton to form a new, highly resonance-stabilized enolate
    anion. Aqueous acid (e.g. sulfuric acid or phosphoric acid) is added in the final step to neutralize
    the enolate and any base still present. The newly formed -keto ester or -diketone is then
    isolated. Note that the reaction requires a stoichiometric amount of base as the removal of the
    doubly -proton thermodynamically drives the otherwise endergonic reaction. That is, Claisen
    condensation does not work with substrates having only one -hydrogen because of the driving
    force effect of deprotonation of the -keto ester in the last step.

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